Sodium Bicarbonate → HCID 11224264, compound

HRID 130510Notes

Reaction equation

HRID 130510 reaction equation
Cl.C(OCC)(=O)C.[CH2:8]([O:10][C:11]([C@:13]1([NH:35]C(OC(C)(C)C)=O)[C@H:18]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)[CH2:17][C@@H:16]2[C@H:14]1[C@@:15]2([F:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:12])[CH3:9].C(=O)([O-])O.[Na+]>>[CH2:8]([O:10][C:11]([C@:13]1([NH2:35])[C@H:18]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)[CH2:17][C@@H:16]2[C@H:14]1[C@@:15]2([F:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:12])[CH3:9]

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 66628528HCID 66628528, compound

Product 1

HCID 11224264HCID 11224264, compoundYield 92.3%

Procedure

2.8 mL of a solution of 4N hydrogen chloride/ethyl acetate was added to 28 mg of (1R,2R,3R,5R,6R)-2-t-butoxycarbonylamino-3-(3,4-dichlorobenzylamino)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester, and the mixture was stirred for 6 hours at ice-cooling and further stirred for 18 hours at room temperature. The reaction solution was ice-cooled and then neutralized with a saturated aqueous solution of sodium hydrogen carbonate, followed by separation. The aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. The desiccant was filtered off, and the filtrate was concentrated under reduced pressure, thereby yielding 21 mg of (1R,2R,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzylamino)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester.

Workup

  1. temperaturecooling
  2. stirringfurther stirred for 18 hours at room temperature
  3. temperaturecooled
  4. customfollowed by separation
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe desiccant was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-36a86bdccae04fe585bd38cbc73a7c59
Source dataset
uspto-grants-2008_06
Patent number
US07381746B2

Reaction notes

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